(E,2S,6S)-8-(4-methoxybenzyloxy)-2,6-di(tert-butyldimethylsilyloxy)oct-4-enenitrile

Base Information

Chemical Name:(E,2S,6S)-8-(4-methoxybenzyloxy)-2,6-di(tert-butyldimethylsilyloxy)oct-4-enenitrile
CAS No.:1254331-84-4
Molecular Formula:C₂₈H₄₉NO₄Si₂
Molecular Weight:519.872
Hs Code.:

Synonyms:(E,2S,6S)-8-(4-methoxybenzyloxy)-2,6-di(tert-butyldimethylsilyloxy)oct-4-enenitrile

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Chemical Property of (E,2S,6S)-8-(4-methoxybenzyloxy)-2,6-di(tert-butyldimethylsilyloxy)oct-4-enenitrile

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Technology Process of (E,2S,6S)-8-(4-methoxybenzyloxy)-2,6-di(tert-butyldimethylsilyloxy)oct-4-enenitrile

There total 5 articles about (E,2S,6S)-8-(4-methoxybenzyloxy)-2,6-di(tert-butyldimethylsilyloxy)oct-4-enenitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

: 1254331-83-3
(S)-4-(4-methoxybenzyloxy)-2-(tert-butyldimethylsilyloxy)butanal

: 1254331-72-0
(S)-2-(tert-butyldimethylsilyloxy)-4-(1-phenyl-1H-tetrazol-5-ylsulfonyl)butanenitrile

: 1254331-84-4
(E,2S,6S)-8-(4-methoxybenzyloxy)-2,6-di(tert-butyldimethylsilyloxy)oct-4-enenitrile

Guidance literature:: (S)-2-(tert-butyldimethylsilyloxy)-4-(1-phenyl-1H-tetrazol-5-ylsulfonyl)butanenitrile; With potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 0.75h;

(S)-4-(4-methoxybenzyloxy)-2-(tert-butyldimethylsilyloxy)butanal; In tetrahydrofuran; at -78 ℃; for 3h; stereoselective reaction;
DOI:10.1021/ol1021417

Reference yield: 85.0%

: 1254331-83-3
(S)-4-(4-methoxybenzyloxy)-2-(tert-butyldimethylsilyloxy)butanal

: C₁₇H₂₅N₅O₃SSi

: 1254331-84-4
(E,2S,6S)-8-(4-methoxybenzyloxy)-2,6-di(tert-butyldimethylsilyloxy)oct-4-enenitrile

Guidance literature:: C₁₇H₂₅N₅O₃SSi; In tetrahydrofuran; at -78 ℃; for 0.75h; Inert atmosphere;

(S)-4-(4-methoxybenzyloxy)-2-(tert-butyldimethylsilyloxy)butanal; With potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 3h; Inert atmosphere;
DOI:10.1021/acs.joc.8b02034

Reference yield:

: 1254331-93-5
(S)-4-(4-methoxybenzyloxy)-2-hydroxybutanenitrile

: 1254331-84-4
(E,2S,6S)-8-(4-methoxybenzyloxy)-2,6-di(tert-butyldimethylsilyloxy)oct-4-enenitrile

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1H-imidazole / dichloromethane / 24 h / 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / toluene; n-heptane / 9 h / -78 - -10 °C / Inert atmosphere

3.1: tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere

3.2: 3 h / -78 °C / Inert atmosphere

With 1H-imidazole; diisobutylaluminium hydride; In tetrahydrofuran; n-heptane; dichloromethane; toluene; 3.1: |Julia-Kocienski Olefination / 3.2: |Julia-Kocienski Olefination;
DOI:10.1021/acs.joc.8b02034